GB1349790A - Process for making polyimide prepolymer and product produced thereby - Google Patents
Process for making polyimide prepolymer and product produced therebyInfo
- Publication number
- GB1349790A GB1349790A GB2329571*A GB2329571A GB1349790A GB 1349790 A GB1349790 A GB 1349790A GB 2329571 A GB2329571 A GB 2329571A GB 1349790 A GB1349790 A GB 1349790A
- Authority
- GB
- United Kingdom
- Prior art keywords
- curable
- prepolymer
- compounds
- april
- mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000004642 Polyimide Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 229920001721 polyimide Polymers 0.000 title abstract 2
- -1 arylene diamine Chemical class 0.000 abstract 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 abstract 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 239000000178 monomer Substances 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 1
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 abstract 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004698 Polyethylene Substances 0.000 abstract 1
- 239000004743 Polypropylene Substances 0.000 abstract 1
- 239000004793 Polystyrene Substances 0.000 abstract 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 abstract 1
- 239000010425 asbestos Substances 0.000 abstract 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 abstract 1
- 239000011324 bead Substances 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000006229 carbon black Substances 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 229910052570 clay Inorganic materials 0.000 abstract 1
- 239000008199 coating composition Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 229930003836 cresol Natural products 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 239000003365 glass fiber Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- 238000010030 laminating Methods 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 239000000206 moulding compound Substances 0.000 abstract 1
- 150000002976 peresters Chemical class 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 229920003192 poly(bis maleimide) Polymers 0.000 abstract 1
- 229920002492 poly(sulfone) Polymers 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 229920000573 polyethylene Polymers 0.000 abstract 1
- 229920001155 polypropylene Polymers 0.000 abstract 1
- 229920001296 polysiloxane Polymers 0.000 abstract 1
- 229920002223 polystyrene Polymers 0.000 abstract 1
- 229920002635 polyurethane Polymers 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 abstract 1
- 239000010453 quartz Substances 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229910052895 riebeckite Inorganic materials 0.000 abstract 1
- 239000004576 sand Substances 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- 125000005591 trimellitate group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
- C08G73/121—Preparatory processes from unsaturated precursors and polyamines
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
1349790 Polyimides of unsaturated anhydrides GENERAL ELECTRIC CO 19 April 1971 [6 April 1970] 23295/71 Headings C3R and C3P A method for preparing curable resins comprises (1) heating at 80 to 200 C. a mixture comprising (A) 0À5 to 2 moles of an arylene diamine per mole of (B) an aliphatically unsaturated dicarboxylic anhydride, (C) a hydrocarbon solvent and (D) cresylic acid (i.e. mixed cresol isomers) or a mixture thereof with phenol, (2) separating a hydrocarbon solventwater azeotrope, and (3) recovering a curable condensation product of (A) and (B). In modifications a minor proportion of (A) may be replaced by a monoamine and up to 10 mol. per cent of (B) by a dianhydride. Preferred solvents (C) have boiling points between 110 and 170 C. The curable prepolymer may be recovered by pouring into a precipitant or the reaction solution may be used to cast films or treat substrates. The prepolymer may be mixed with fillers, e.g. clay, quartz, silica, sand, carbon black, glass fibres or beads, carbon fibre or asbestos; olefinic monomers, e.g. styrene, bismaleimide, N-phenyl maleimide, divinyl benzene ortriallylcyanurate or trimellitate; polymers e.g. P.V.C., polyethylene, polypropylene, polystyrene, polysulphones, polyurethanes, silicones or polyesters; solvents, e.g. N-methylpyrrolidone, dimethylacetamide, toluene or ethylene dichloride; and plasticizers, e.g. dialkylphthalate. The curable polymer or blend thereof with olefinic monomer may be cured at 50 to 300 C. using free radical initiators, various peroxides, per-esters and azo compounds being specified; irradiation with high energy electrons, X-rays or U.V. light may also be applied. They may be used for laminating compounds, moulding compounds and coating compositions.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2607970A | 1970-04-06 | 1970-04-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1349790A true GB1349790A (en) | 1974-04-10 |
Family
ID=21829762
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2329571*A Expired GB1349790A (en) | 1970-04-06 | 1971-04-19 | Process for making polyimide prepolymer and product produced thereby |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3678015A (en) |
| CA (1) | CA924435A (en) |
| DE (1) | DE2114924A1 (en) |
| FR (1) | FR2085880B1 (en) |
| GB (1) | GB1349790A (en) |
| IL (1) | IL36338A0 (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3868351A (en) * | 1970-12-02 | 1975-02-25 | Gen Electric | Solution process for the preparation of polyimdies from diamines and anhydrides |
| US3714131A (en) * | 1971-08-11 | 1973-01-30 | Gen Electric | Polyamideimides |
| US3996203A (en) * | 1972-09-13 | 1976-12-07 | General Electric Company | Solution process for the preparation of polyimides from diamines and anhydrides |
| US3998786A (en) * | 1973-05-25 | 1976-12-21 | University Of Notre Dame Du Lac | Process for preparing aromatic polyimides, polyimides prepared thereby |
| GB1587820A (en) * | 1976-10-04 | 1981-04-08 | Tba Industrial Products Ltd | Manufacture of moulding materials |
| EP0172274B1 (en) * | 1984-06-26 | 1989-05-10 | Toray Industries, Inc. | A method for preparing polyimide prepolymers |
| CN105348530B (en) * | 2015-12-02 | 2017-08-25 | 河北麦格尼菲复合材料股份有限公司 | A kind of preparation method of bimaleimide resin prepolymerization system for liquid condition shaping technology |
| JP6835864B2 (en) | 2016-02-22 | 2021-02-24 | ビーエイエスエフ・ソシエタス・エウロパエアＢａｓｆ Ｓｅ | Polyamide mixture with pyrrolidone-containing polyamide |
| EP3494153B1 (en) | 2016-08-02 | 2020-09-09 | Basf Se | Transparent tpu blends with pyrrolidone containing polyamides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2174619A (en) * | 1936-09-22 | 1939-10-03 | Du Pont | Polyamides |
| US2306918A (en) * | 1940-02-15 | 1942-12-29 | Research Corp | Amine reaction product |
| SE316011B (en) * | 1964-11-13 | 1969-10-13 | Rhodiaceta | |
| AT279169B (en) * | 1967-01-26 | 1970-02-25 | Rhodiaceta | METHOD FOR PRODUCING A CROSS-LINKED POLYAMIDE RESIN |
-
1970
- 1970-04-06 US US26079A patent/US3678015A/en not_active Expired - Lifetime
-
1971
- 1971-02-24 CA CA106125A patent/CA924435A/en not_active Expired
- 1971-03-03 IL IL36338A patent/IL36338A0/en unknown
- 1971-03-27 DE DE19712114924 patent/DE2114924A1/en active Pending
- 1971-04-06 FR FR7112184A patent/FR2085880B1/fr not_active Expired
- 1971-04-19 GB GB2329571*A patent/GB1349790A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA924435A (en) | 1973-04-10 |
| IL36338A0 (en) | 1971-05-26 |
| FR2085880B1 (en) | 1973-10-19 |
| DE2114924A1 (en) | 1971-10-21 |
| US3678015A (en) | 1972-07-18 |
| FR2085880A1 (en) | 1971-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |